CA2563959C - (1,10b-dihydro-2-(aminocarbonyl-phenyl)-5h-pyrazolo[1,5-c][1,3]benzoxazin-5-yl)phenyl methanone derivatives as hiv viral replication inhibitors - Google Patents
(1,10b-dihydro-2-(aminocarbonyl-phenyl)-5h-pyrazolo[1,5-c][1,3]benzoxazin-5-yl)phenyl methanone derivatives as hiv viral replication inhibitors Download PDFInfo
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- CA2563959C CA2563959C CA2563959A CA2563959A CA2563959C CA 2563959 C CA2563959 C CA 2563959C CA 2563959 A CA2563959 A CA 2563959A CA 2563959 A CA2563959 A CA 2563959A CA 2563959 C CA2563959 C CA 2563959C
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- 229940123627 Viral replication inhibitor Drugs 0.000 title description 2
- CBJVVHOEVDZONM-UHFFFAOYSA-N 2-(5-benzoyl-5,10b-dihydro-1h-pyrazolo[1,5-c][1,3]benzoxazin-2-yl)benzamide Chemical class NC(=O)C1=CC=CC=C1C1=NN2C(C(=O)C=3C=CC=CC=3)OC3=CC=CC=C3C2C1 CBJVVHOEVDZONM-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 203
- -1 5H-pyrazolo[1,5-c] [1,3]benzoxazin-5-yl Chemical group 0.000 claims abstract description 155
- 239000003814 drug Substances 0.000 claims abstract description 18
- 125000003118 aryl group Chemical group 0.000 claims description 88
- 125000001424 substituent group Chemical group 0.000 claims description 80
- 125000000623 heterocyclic group Chemical group 0.000 claims description 53
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 50
- 125000003277 amino group Chemical group 0.000 claims description 39
- 125000003386 piperidinyl group Chemical group 0.000 claims description 33
- 125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 claims description 30
- 229920006395 saturated elastomer Polymers 0.000 claims description 30
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 29
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 26
- 125000005843 halogen group Chemical group 0.000 claims description 25
- 229910052757 nitrogen Inorganic materials 0.000 claims description 24
- 150000003839 salts Chemical class 0.000 claims description 24
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 23
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 23
- 125000002757 morpholinyl group Chemical group 0.000 claims description 22
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 19
- 125000004193 piperazinyl group Chemical group 0.000 claims description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 18
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 17
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- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 12
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- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 9
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 8
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- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 4
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- 125000004607 1,2,3,4-tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims description 3
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- 125000002098 pyridazinyl group Chemical group 0.000 claims description 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 45
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 14
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- HXPVVRJJQALEHM-UHFFFAOYSA-N 4-[5-(4-fluorobenzoyl)-5,10b-dihydro-1h-pyrazolo[1,5-c][1,3]benzoxazin-2-yl]-n-[(4-methoxyphenyl)methyl]-n-methylbenzamide Chemical compound C1=CC(OC)=CC=C1CN(C)C(=O)C1=CC=C(C=2CC3N(C(OC4=CC=CC=C43)C(=O)C=3C=CC(F)=CC=3)N=2)C=C1 HXPVVRJJQALEHM-UHFFFAOYSA-N 0.000 claims 1
- BTMJCCYNKNLBSU-UHFFFAOYSA-N 4-[5-(4-tert-butylbenzoyl)-5,10b-dihydro-1h-pyrazolo[1,5-c][1,3]benzoxazin-2-yl]-n-cyclopentylbenzamide Chemical compound C1=CC(C(C)(C)C)=CC=C1C(=O)C1N2N=C(C=3C=CC(=CC=3)C(=O)NC3CCCC3)CC2C2=CC=CC=C2O1 BTMJCCYNKNLBSU-UHFFFAOYSA-N 0.000 claims 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 1
- ZZOHFMGBBCQRPL-UHFFFAOYSA-N n-cyclopentyl-4-[5-(4-ethylbenzoyl)-5,10b-dihydro-1h-pyrazolo[1,5-c][1,3]benzoxazin-2-yl]benzamide Chemical compound C1=CC(CC)=CC=C1C(=O)C1N2N=C(C=3C=CC(=CC=3)C(=O)NC3CCCC3)CC2C2=CC=CC=C2O1 ZZOHFMGBBCQRPL-UHFFFAOYSA-N 0.000 claims 1
- RNEVIDDMGJLZHR-UHFFFAOYSA-N n-cyclopentyl-4-[5-(4-methylsulfonylbenzoyl)-5,10b-dihydro-1h-pyrazolo[1,5-c][1,3]benzoxazin-2-yl]benzamide Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C(=O)C1N2N=C(C=3C=CC(=CC=3)C(=O)NC3CCCC3)CC2C2=CC=CC=C2O1 RNEVIDDMGJLZHR-UHFFFAOYSA-N 0.000 claims 1
- RBWWHWFHQIGHPM-UHFFFAOYSA-N n-cyclopentyl-4-[5-(4-nitrobenzoyl)-5,10b-dihydro-1h-pyrazolo[1,5-c][1,3]benzoxazin-2-yl]benzamide Chemical compound C1=CC([N+](=O)[O-])=CC=C1C(=O)C1N2N=C(C=3C=CC(=CC=3)C(=O)NC3CCCC3)CC2C2=CC=CC=C2O1 RBWWHWFHQIGHPM-UHFFFAOYSA-N 0.000 claims 1
- VLBMNFXCXWDESX-UHFFFAOYSA-N n-cyclopentyl-4-[5-(4-propylbenzoyl)-5,10b-dihydro-1h-pyrazolo[1,5-c][1,3]benzoxazin-2-yl]benzamide Chemical compound C1=CC(CCC)=CC=C1C(=O)C1N2N=C(C=3C=CC(=CC=3)C(=O)NC3CCCC3)CC2C2=CC=CC=C2O1 VLBMNFXCXWDESX-UHFFFAOYSA-N 0.000 claims 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims 1
- 241000725303 Human immunodeficiency virus Species 0.000 abstract description 22
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- LEVJVKGPFAQPOI-UHFFFAOYSA-N phenylmethanone Chemical class O=[C]C1=CC=CC=C1 LEVJVKGPFAQPOI-UHFFFAOYSA-N 0.000 abstract description 2
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- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 229920000447 polyanionic polymer Polymers 0.000 description 1
- 125000006684 polyhaloalkyl group Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 239000000651 prodrug Substances 0.000 description 1
- 229940002612 prodrug Drugs 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 108010043277 recombinant soluble CD4 Proteins 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000004043 responsiveness Effects 0.000 description 1
- 229960000311 ritonavir Drugs 0.000 description 1
- NCDNCNXCDXHOMX-XGKFQTDJSA-N ritonavir Chemical compound N([C@@H](C(C)C)C(=O)N[C@H](C[C@H](O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1SC=NC=1)CC=1C=CC=CC=1)C(=O)N(C)CC1=CSC(C(C)C)=N1 NCDNCNXCDXHOMX-XGKFQTDJSA-N 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 229960001852 saquinavir Drugs 0.000 description 1
- QWAXKHKRTORLEM-UGJKXSETSA-N saquinavir Chemical compound C([C@@H]([C@H](O)CN1C[C@H]2CCCC[C@H]2C[C@H]1C(=O)NC(C)(C)C)NC(=O)[C@H](CC(N)=O)NC(=O)C=1N=C2C=CC=CC2=CC=1)C1=CC=CC=C1 QWAXKHKRTORLEM-UGJKXSETSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000013595 supernatant sample Substances 0.000 description 1
- 239000002511 suppository base Substances 0.000 description 1
- FIAFUQMPZJWCLV-UHFFFAOYSA-N suramin Chemical compound OS(=O)(=O)C1=CC(S(O)(=O)=O)=C2C(NC(=O)C3=CC=C(C(=C3)NC(=O)C=3C=C(NC(=O)NC=4C=C(C=CC=4)C(=O)NC=4C(=CC=C(C=4)C(=O)NC=4C5=C(C=C(C=C5C(=CC=4)S(O)(=O)=O)S(O)(=O)=O)S(O)(=O)=O)C)C=CC=3)C)=CC=C(S(O)(=O)=O)C2=C1 FIAFUQMPZJWCLV-UHFFFAOYSA-N 0.000 description 1
- 229960005314 suramin Drugs 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 238000007910 systemic administration Methods 0.000 description 1
- 229960004556 tenofovir Drugs 0.000 description 1
- BEUUJDAEPJZWHM-COROXYKFSA-N tert-butyl n-[(2s,3s,5r)-3-hydroxy-6-[[(2s)-1-(2-methoxyethylamino)-3-methyl-1-oxobutan-2-yl]amino]-6-oxo-1-phenyl-5-[(2,3,4-trimethoxyphenyl)methyl]hexan-2-yl]carbamate Chemical compound C([C@@H]([C@@H](O)C[C@H](C(=O)N[C@H](C(=O)NCCOC)C(C)C)CC=1C(=C(OC)C(OC)=CC=1)OC)NC(=O)OC(C)(C)C)C1=CC=CC=C1 BEUUJDAEPJZWHM-COROXYKFSA-N 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 229960000838 tipranavir Drugs 0.000 description 1
- SUJUHGSWHZTSEU-FYBSXPHGSA-N tipranavir Chemical compound C([C@@]1(CCC)OC(=O)C([C@H](CC)C=2C=C(NS(=O)(=O)C=3N=CC(=CC=3)C(F)(F)F)C=CC=2)=C(O)C1)CC1=CC=CC=C1 SUJUHGSWHZTSEU-FYBSXPHGSA-N 0.000 description 1
- 229950011282 tivirapine Drugs 0.000 description 1
- 238000002723 toxicity assay Methods 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 241001430294 unidentified retrovirus Species 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 230000009385 viral infection Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5375—1,4-Oxazines, e.g. morpholine
- A61K31/538—1,4-Oxazines, e.g. morpholine ortho- or peri-condensed with carbocyclic ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP04101913.4 | 2004-05-04 | ||
| EP04101913 | 2004-05-04 | ||
| US60427504P | 2004-08-25 | 2004-08-25 | |
| US60/604,275 | 2004-08-25 | ||
| PCT/EP2005/052041 WO2005105810A2 (en) | 2004-05-04 | 2005-05-04 | (1,10b-dihydro-2-(aminocarbonyl-phenyl)-5h-pyrazolo[1,5- c][1,3]benzoxazin-5-yl)phenyl methanone derivatives as hiv viral replication inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2563959A1 CA2563959A1 (en) | 2005-11-10 |
| CA2563959C true CA2563959C (en) | 2014-07-15 |
Family
ID=35058129
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2563959A Expired - Fee Related CA2563959C (en) | 2004-05-04 | 2005-05-04 | (1,10b-dihydro-2-(aminocarbonyl-phenyl)-5h-pyrazolo[1,5-c][1,3]benzoxazin-5-yl)phenyl methanone derivatives as hiv viral replication inhibitors |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US7326703B2 (de) |
| EP (1) | EP1778696B1 (de) |
| JP (1) | JP4929162B2 (de) |
| KR (1) | KR20070015547A (de) |
| CN (1) | CN1950380B (de) |
| AP (1) | AP2006003759A0 (de) |
| AR (1) | AR048650A1 (de) |
| AT (1) | ATE389660T1 (de) |
| AU (1) | AU2005238235B2 (de) |
| BR (1) | BRPI0510612A (de) |
| CA (1) | CA2563959C (de) |
| DE (1) | DE602005005490T2 (de) |
| ES (1) | ES2303244T3 (de) |
| IL (1) | IL178082A (de) |
| MX (1) | MXPA06012755A (de) |
| NO (1) | NO20065582L (de) |
| PL (1) | PL1778696T3 (de) |
| RU (1) | RU2382789C2 (de) |
| WO (1) | WO2005105810A2 (de) |
| ZA (1) | ZA200609178B (de) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7122185B2 (en) | 2002-02-22 | 2006-10-17 | Progenics Pharmaceuticals, Inc. | Anti-CCR5 antibody |
| TW200710091A (en) * | 2005-04-11 | 2007-03-16 | Tibotec Pharm Ltd | (1,10B-dihydro-2-(aminoalkyl-phenyl)-5H-pyrazolo [1,5-c][1,3]benzoxazin-5-yl)phenyl methanone derivatives as HIV viral replication inhibitors |
| CA2616189C (en) * | 2005-07-22 | 2019-03-26 | Progenics Pharmaceuticals, Inc. | Methods for reducing viral load in hiv-1-infected patients |
| JP2010531301A (ja) * | 2007-06-25 | 2010-09-24 | テイボテク・フアーマシユーチカルズ | ダルナビル及びエトラビリンを含んでなる組み合わせ調剤 |
| US8592487B2 (en) * | 2007-10-26 | 2013-11-26 | Concert Pharmaceuticals, Inc. | Deuterated darunavir |
| WO2009134401A2 (en) * | 2008-04-29 | 2009-11-05 | Progenics Pharmaceuticals, Inc. | Methods of inhibiting infection by diverse subtypes of drug-resistant hiv-1 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5145684A (en) | 1991-01-25 | 1992-09-08 | Sterling Drug Inc. | Surface modified drug nanoparticles |
| DE4210939A1 (de) * | 1992-04-02 | 1993-10-07 | Bayer Ag | Verwendung von 7-Oxo-7H-pyrido[1,2,3-de][1,4]benzoxacin-6-carbonsäuren und -estern als Arzneimittel |
| IL106507A (en) * | 1992-08-07 | 1997-11-20 | Merck & Co Inc | Pharmaceutical compositions containing benzoxazinones and some novel compounds of this type |
| PH30929A (en) | 1992-09-03 | 1997-12-23 | Janssen Pharmaceutica Nv | Beads having a core coated with an antifungal and a polymer. |
| PT721331E (pt) | 1993-10-01 | 2002-05-31 | Astrazeneca Ab | Processo i |
| WO1997044014A1 (en) | 1996-05-20 | 1997-11-27 | Janssen Pharmaceutica N.V. | Antifungal compositions with improved bioavailability |
| ES2203790T3 (es) * | 1996-10-02 | 2004-04-16 | Bristol-Myers Squibb Pharma Company | 1,4-dihidro-2h-3,1-benzoxacin-2-onas 4,4-disustituidas utiles como inhibidores de la transcriptasa reversa del hiv e intermedios y procedimientos para su preparacion. |
| SK284813B6 (sk) | 1997-03-26 | 2005-12-01 | Janssen Pharmaceutica N. V. | Peleta obsahujúca itrakonazol, spôsob jej prípravy a farmaceutická dávková forma s jej obsahom |
| BR9815899A (pt) * | 1998-05-20 | 2001-02-20 | Lilly Co Eli | Compostos antivirais |
| IL157875A0 (en) * | 2001-04-10 | 2004-03-28 | Pfizer | Pyrazole derivatives for treating hiv |
-
2005
- 2005-05-03 AR ARP050101767A patent/AR048650A1/es unknown
- 2005-05-04 WO PCT/EP2005/052041 patent/WO2005105810A2/en not_active Ceased
- 2005-05-04 PL PL05740229T patent/PL1778696T3/pl unknown
- 2005-05-04 AU AU2005238235A patent/AU2005238235B2/en not_active Ceased
- 2005-05-04 ES ES05740229T patent/ES2303244T3/es not_active Expired - Lifetime
- 2005-05-04 DE DE602005005490T patent/DE602005005490T2/de not_active Expired - Lifetime
- 2005-05-04 JP JP2007512194A patent/JP4929162B2/ja not_active Expired - Fee Related
- 2005-05-04 RU RU2006142705/04A patent/RU2382789C2/ru not_active IP Right Cessation
- 2005-05-04 US US11/568,380 patent/US7326703B2/en not_active Expired - Fee Related
- 2005-05-04 CA CA2563959A patent/CA2563959C/en not_active Expired - Fee Related
- 2005-05-04 BR BRPI0510612-5A patent/BRPI0510612A/pt not_active IP Right Cessation
- 2005-05-04 AT AT05740229T patent/ATE389660T1/de not_active IP Right Cessation
- 2005-05-04 MX MXPA06012755A patent/MXPA06012755A/es active IP Right Grant
- 2005-05-04 KR KR1020067022005A patent/KR20070015547A/ko not_active Withdrawn
- 2005-05-04 CN CN2005800140097A patent/CN1950380B/zh not_active Expired - Fee Related
- 2005-05-04 EP EP05740229A patent/EP1778696B1/de not_active Expired - Lifetime
- 2005-05-04 AP AP2006003759A patent/AP2006003759A0/xx unknown
-
2006
- 2006-09-14 IL IL178082A patent/IL178082A/en not_active IP Right Cessation
- 2006-11-03 ZA ZA200609178A patent/ZA200609178B/xx unknown
- 2006-12-04 NO NO20065582A patent/NO20065582L/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CN1950380A (zh) | 2007-04-18 |
| ATE389660T1 (de) | 2008-04-15 |
| JP4929162B2 (ja) | 2012-05-09 |
| AP2006003759A0 (en) | 2006-10-31 |
| DE602005005490T2 (de) | 2009-04-23 |
| ES2303244T3 (es) | 2008-08-01 |
| EP1778696A2 (de) | 2007-05-02 |
| US20070248624A1 (en) | 2007-10-25 |
| RU2382789C2 (ru) | 2010-02-27 |
| JP2007536346A (ja) | 2007-12-13 |
| AU2005238235B2 (en) | 2011-07-07 |
| DE602005005490D1 (de) | 2008-04-30 |
| BRPI0510612A (pt) | 2007-10-30 |
| CN1950380B (zh) | 2010-12-08 |
| IL178082A0 (en) | 2006-12-31 |
| EP1778696B1 (de) | 2008-03-19 |
| CA2563959A1 (en) | 2005-11-10 |
| AU2005238235A1 (en) | 2005-11-10 |
| MXPA06012755A (es) | 2007-01-16 |
| IL178082A (en) | 2012-06-28 |
| KR20070015547A (ko) | 2007-02-05 |
| AR048650A1 (es) | 2006-05-10 |
| ZA200609178B (en) | 2008-08-27 |
| WO2005105810A2 (en) | 2005-11-10 |
| PL1778696T3 (pl) | 2008-08-29 |
| RU2006142705A (ru) | 2008-06-20 |
| NO20065582L (no) | 2006-12-04 |
| WO2005105810A3 (en) | 2006-03-02 |
| US7326703B2 (en) | 2008-02-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20170504 |